Rogeni Misaelle M.

Petinglay Date submitted: March 27, 2017

B.S. in Chemistry

EXPERIMENT 6
INTRODUCTION TO STEREOCHEMISTRY

Chirality, Enantiomerism, Diastereomerism and Optical Activity

1. Determine whether the following pairs of objects are superimposable or not superimposable
with each other.
a) two forks Superimposable
b) your left hand and your right hand Not superimposable

2. Yes or No. View your right hand in front of the mirror

a) Is the reflection of your right hand superimposable on your left hand? Yes
b) Is your right hand the mirror image of your left hand? Yes

3. Using a mirror, decide whether the following objects are superimposable or not
superimposable on their mirror images.
a) a fork Superimposable
b) a pentagon Superimposable
c) your left hand Not superimposable

4. Yes or No. Tell whether the following objects contain at least one plane of symmetry.
a) a sphere Yes
b) a regular tetrahedron Yes
c) a shoe No

5. Determine whether the objects in No. 4 are superimposable or not superimposable on their
mirror images.
a) a sphere Superimposable
b) a regular tetrahedron Superimposable
c) a shoe Not superimposable

6. Describe the relationship between the presence of a plane of symmetry in an object and the
objects superimposability on its mirror image in your own words.
Answer: The presence of a plane of symmetry means that the object is superimposable because
one half of the object is exactly a reflection of the other half. Thus, the mirror image is align with
all parts of the object.

7. Look for the model of CH4. Is it chiral or achiral? Why?

Answer: CH4 is achiral because it is superimposable on its mirror image.

8. Look for the model of CBrFClH. Is it chiral or achiral? Why?

Anwser: CBrFClH is chiral because it is non-superimposable on its mirror image.
9. a) Are enantiomers chiral? Yes
b) Do enantiomers have the same molecular formula? Yes
c) Does one structural formula represent both members No
of a pair of enantiomers?

10. Are enantiomers stereoisomers?

Answer: Yes.

11. Determine whether each of the following are optically active or optically inactive.
a) CH3CH(NH2)COOH optically active
b) CH3CH2CHClCH3 optically active
c) CH3CH2CH2CH3 optically inactive

12. Which enantiomer of alanine rotates the plane polarized light clockwise?
Answer: (+)-alanine

13. Which of the following aqueous solutions are likely to be optically inactive?
a) a solution of ethanol, CH3CH2OH optically active
b) a solution of (+) alanine optically active
c) a solution of (-) alanine optically active
d) a solution containing equimolar quantities of (+) optically inactive
alanine and (-) alanine

14. How is the racemic mixture of alanine represented?

Answer: A solution containing equimolar quantities of (+) alanine and (-) alanine. This is
represented as (+/-) alanine.

15. Examine the models for the presence of a plane of symmetry. Which of them has at least one
plane of symmetry?

Answer: a and b

16. Which are superimposable on their mirror image?

Answer: a and b

17. Which model represents a chiral molecule?

Answer: c and d
18. How many different atoms or groups of atoms must be attached to the central carbon atom in
order to confer chirality to the molecule?
Answer: 4 different atoms or group of atoms

Consider the following structural formula for Nos. 19-20

19. Which is a chiral molecule?

Answer: a

20. Which can exist as a pair of enantiomers? Draw the pair of enantiomers.

COOH CH3 CH3

Now we will consider molecules with more than one chiral center. Consider 2,3-
dihydroxybutanoic acid.

The flying wedge representation of 2,3-dihydroxybutanoic acid is shown below.

 COOH

OH
22. a) Draw the flying wedge representation of its mirror image (II) OH

b) Are I and II chiral? Answer: Yes CH3

A compound which contains two different chiral centers can exist as four optically active
stereoisomers. The flying wedge representation of the four stereoisomeric 2,3-dihydroxybutanoic
acid are given below.

23. What is the relationship between?

a) I and II Enantiomers
b) III and IV Enantiomers
c) I and IV Diastereomers
d) II and IV Diastereomers

24. What is the relationship between?

a) I and III Diastereomers
b) II and III Diastereomers

OPEN CHAIN COMPOUNDS

25. Look for the model of ethane. Rotate the C C single bond.
a) Is there a change in the relative positions of the different atoms Yes
as the C-C bond is rotated?
b) Does the ethane molecule have more than one conformation? Yes

26. In which extreme conformation are the hydrogens farthest apart from each other?
Answer: Staggered conformation

27. Draw the Newman and Sawhorse representation of ethane with the highest potential energy.
28. Draw the Newman and Sawhorse representation of ethane with the lowest potential energy.

29. Which is the preferred conformation of ethane?

Answer: Staggered conformation

30. Look at the model of chloroethane.

a) Do all chloroethane molecules spend all of their time in this No
preferred conformation?
b) What is the preferred conformation called? Staggered conformation

RING COMPOUNDS

31. Look at the model of cyclohexane. Rotate the carbon atoms and examine the different
conformations
a) Are there any conformations in which all carbon atoms of the ring are in one plane?
Answer: No. Cyclohexane has no flat form.

32. Does flipping of carbon 4 result in a change in conformation?

Answer: Yes

33. In which conformations are the hydrogens farthest apart?

Answer: Chair (staggered) conformation

34. Which is the preferred conformation?

Answer: Chair (staggered) conformation

Compare your models with the Newman Projections below by looking through the C2
C3 and C5 C6 bonds at the same time.
35. Which is the eclipsed conformation?
Answer: II

36. Which is the staggered conformation?

Answer: I

37. Mark the axial bonds. Hold carbon atoms 1, 2, 3, 4, 5, and 6 firmly and flip up carbon 4.
What is the resulting conformation?
Answer: Chair conformation

38. Then holding carbons 2, 3, 4, 5, and 6 firmly, flip down carbon 1. What is now the resulting
conformation?
Answer: Chair conformation

39. Did you break any bonds?

Answer: No

40. What is the orientation of the marked bonds now?

Answer: Equatorial bonds

41. Make a sketch of the final conformation showing the marked bonds.

42. Represent the process using the symbol ( ) to indicate that the two chair conformations are
in dynamic equilibrium.
43. Construct a model of methylcyclohexane with the methyl attached axially. Make the ring
undergo inversion and complete the following:

Answer:

CH3

44.
a) In which chair conformation (a or b) is the methyl group farthest from the neighboring
hydrogen atom?
Answer: b
b) In which chair conformation (a or b) does the methyl group have greater room?
Answer: b
c) Which is the preferred conformation of methylcyclohexane (a or b)?
Answer:b

45. Make a general statement about the preferred conformation of monosubstituted

cyclohexanes.
Answer:
Conformations that maximize those repulsive forces between each atom are what
monosubstituted cyclohexanes prefer. This type of conformations are the stable ones, therefore
less energy is needed in each atom. This is called the staggered conformation.